Water → ethyl 1-{[4-(3-acetylphenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylate

HRID 1257342Notes

Reaction equation

HRID 1257342 reaction equation
Br[C:2]1[N:3]=[C:4]([CH2:7][N:8]2[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[N:9]2)[S:5][CH:6]=1.[C:18]([C:21]1[CH:22]=[C:23](B(O)O)[CH:24]=[CH:25][CH:26]=1)(=[O:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:18]([C:21]1[CH:26]=[C:25]([C:2]2[N:3]=[C:4]([CH2:7][N:8]3[CH:12]=[C:11]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[N:9]3)[S:5][CH:6]=2)[CH:24]=[CH:23][CH:22]=1)(=[O:20])[CH3:19]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343103-Acetylphenylboronic acidHCID 58127892ethyl 1-[(4-bromo-1,3-thiazol-2-yl)methyl]-1H-pyrazole-4-carboxylate

Product 1

HCID 58127487ethyl 1-{[4-(3-acetylphenyl)-1,3-thiazol-2-yl]methyl}-1H-pyrazole-4-carboxylateYield 67%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
120 °C

Procedure

Under an argon atmosphere, to a solution (4 mL) of the compound (250 mg, 0.79 mmol) obtained in Example 30c in 1,2-dimethoxyethane were added (3-acetylphenyl)boronic acid (156 mg, 0.95 mmol), potassium carbonate (218 mg, 1.58 mmol) and tetrakistriphenylphosphinepalladium (91 mg, 0.079 mmol), and the mixture was stirred at 120° C. for 15 min under microwave conditions. The mixture was allowed to cool to room temperature, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=1/1) to give the title compound (188 mg, 67%) as a pale-brown oil.

Workup

  1. temperatureto cool to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained crude product
  7. customwas purified by column chromatography (hexane-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-06dc9de19fe84b49830064949771c52e
Source dataset
uspto-grants-2013_06
Patent number
US08461348B2

Reaction notes

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